How to Finally Conquer That Dreaded To-Do List Item

Jessica Stillman is a freelance writer based in Cyprus with interests in unconventional career paths, generational differences, and the future of work. She has blogged for CBS MoneyWatch, GigaOM, and Brazen Careerist.

You may be the most conscientious and hard-working business owner out there, but it’s still almost certain you have That Task.

You know the one--it needs doing, but it’s just so dreary, difficult, or plain boring that it sits on your to-do list for weeks as you come up with excuse after excuse to put it off for another day. You could wait until the brink of disaster spurs you to action, but it’s unlikely you’ll do your best work under those circumstances. Is there a better method than procrastination to finally drive you to tackle it?

Don’t Rely on Willpower

The secret to defeating your to-do list nemesis, according to Grant Halvorson, isn’t sheer force of will. Research, she reports, backs up what you’ve probably intuited already: Your willpower is pretty limited. "Studies show that people routinely overestimate their capacity for self-control and rely on it too often to keep them out of hot water," she says.

So what’s the alternative? Instead of trying to muscle your way past your mental block, rely on crafty planning to corner That Task with no hope of escape. In practice, that means getting very specific about your plan well in advance of when you’ll need to take action. Use if-then statements to accomplish this. Grant Halvorson offers a couple of examples:

If it is 2 p.m., then I will stop what I’m doing and start work on the report Bob asked for.

If my boss doesn’t mention my request for a raise at our meeting, then I will bring it up again before the meeting ends.

Why It Works

Why do these sort of specific if-then plans work? They eliminate any wiggle room and give your brain very little opportunity to weasel its way out of once again procrastinating on That Task.

"By deciding in advance exactly what you’re going to do, and when and where you’re going to do it, there’s no deliberating when the time comes," Grant Halvorson explains. "It’s when we deliberate that willpower becomes necessary to make the tough choice. But if-then plans dramatically reduce the demands placed on your willpower, by ensuring that you’ve made the right decision way ahead of the critical moment."

If you’re doubting that such a simple strategy can make an impact on your ability to get your least-loved tasks done, Grant Halvorson points you in the direction of more than 200 studies on its effectiveness. This huge body of research shows that, in fact, if-then planning can "increase rates of goal attainment and productivity by 200 percent to 300 percent, on average."